(R)-4-Benzyl-2-oxazolidinone (HCID 2734969)

Overview

See also: (S)-4-Benzyl-2-oxazolidinone (annotation moved to).

Names & identifiers

Preferred name: (R)-4-Benzyl-2-oxazolidinone
IUPAC: (4R)-4-benzyl-1,3-oxazolidin-2-one
English name: (R)-4-Benzyl-2-oxazolidinone
Molecular formula: C10H11NO2
Molecular weight: 177.2

Names & synonyms

(R)-4-Benzyl-2-oxazolidinone(R)-(+)-4-Benzyl-2-oxazolidinone2-Oxazolidinone, 4-(phenylmethyl)-, (4R)-DTXSID60370594RefChem:407325DTXCID20321628102029-44-7(r)-4-benzyloxazolidin-2-one(4R)-4-benzyl-1,3-oxazolidin-2-oneMFCD00010846(+)-4-benzyl-2-oxazolidinone(4r)-4-(phenylmethyl)-1,3-oxazolidin-2-one

Show more names

(R)-4-(PHENYLMETHYL)-2-OXAZOLIDINONER-BOZRBOX(4R)-4-BENZYLOXAZOLIDIN-2-ONE4-benzyl-2-0xazolidinone(4R)-Phenylmethyl-2-oxazolidinoneMLS00TB-2044

(r)-(-)-4-benzyl-2-oxazolidinone(4r)-4-(phenylmethyl)-2-oxazolidinone4-Benzyl-1,3-oxazolidin-2-one #(R)-4-benzyl-oxazolidin-2-oneNetarsudil Impurity 7r-4-benzyl-2-oxazolidinoneMLS0012428024(R)-benzyl-2-oxazolidinone

Database identifiers

CAS: 102029-44-7
PubChem CID: 2734969
DTXSID: DTXSID60370594
ChEMBL: CHEMBL1366601
UNII: CVS8468YG3
EC Number: 600-264-2
Nikkaji: J462.969H

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 38.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 13
Formal charge: 0
Complexity: 187

Physicochemical properties

Melting point: 88 · 88-90 °C
alpha: 62 · 62 º (C=1, CHCl3)
Boiling point: 309.12 °C · 309.12°C (rough estimate)
Density: 1.1607 · 1.1607 (rough estimate)
refractive index: 14.5 ° · 14.5 ° (C=5, MeOH)
storage temp.: Inert atmosphere,Room Temperature
solubility: Chloroform (Slightly)
pka: 12.78 · 12.78±0.40(Predicted)
form: Crystalline Powder
color: White to almost white
optical activity: 18 · [α]18/D +64°, c = 1 in chloroform
Water Solubility: Insoluble in water. Soluble in Chloroform.
Sensitive: Hygroscopic
BRN: 4782551 · 4782551
InChI: 1S/C10H11NO2/c12-10-11-9(7-13-10)6-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,11,12)/t9-/m1/s1
InChIKey: OJOFMLDBXPDXLQ-SECBINFHSA-N
SMILES: O=C1N[C@@H](CO1)Cc2ccccc2
CAS DataBase Reference: 102029 · 102029-44-7(CAS DataBase Reference)
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 320 · H320
Precautionary statements: 264 · P264-P305+P351+P338+P337+P313
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 22 · 22-24/25-36-26
WGK Germany: 3 · 3
F: 3 · 3-10
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (75%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information(R)-(+)-4-Benzyl-2-oxazolidinone: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesSkin Irrit. 2 (75%)

Safety data

F: 3-10
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29349990
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 22-24/25-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H320
Precautionary statements: P264-P305+P351+P338+P337+P313

Chemistry & industry

Applications · 3 items

Description(R)-4-Benzyl-2-oxazolidinone is a derivative of oxazolidinone. It can be used in the preparation of enantiopure carbocyclic nucleosides, which act as a HIV protease inhibitor. It can also be used as a chiral auxiliary in the enantioselective synthesis of (2R, 2′S)-erythro-methylphenidate, beta-lactams and alpha-amino acids. Its end product includes asymmetric single isomeric drugs such as antitumor, anesthetic and entipasmodic products.

Usesintermediate for Aliskiren hemifumarate, Darifenacin HBr, Zolmitriptan

Uses(R)-(+)-4-Benzyl-2-oxazolidinones are used in the enantioselective synthesis of beta-lactams and alpha-amino acids. End products can include asysmmetric single isomeric drugs of antitumor, anesthetic, antipasmodic products. Used in the synthesis of HIV protease inhibitors. An oxazolidinone used in chiral auxiliary asymetric synthesis.